31 Best Comedy Movies On Max (HBO Max) (Page 2)

This drama was the first feature written and directed by an out Black lesbian, Cheryl Dunye, and it is an absolute joy: a cheeky faux-documentary that ingeniously blends lesbian dating life with a historical dive into Black actors in 30s Hollywood.

Dunye plays Cheryl, a self-effacing version of herself, an aspiring director working at a video store who begins to research an actress known as the Watermelon Woman for a documentary. The more Cheryl dives into her research, the more she sees parallels between her subject and her own relationship. 

As incisive as it is funny, The Watermelon Woman shares some common ground with other major indie debuts of the era like Spike Lee’s She’s Gotta Have It and funnily enough Kevin Smith’s Clerks, but Dunye’s style is wholly her own and a dazzling treat to experience.

 

Genre: Comedy, Drama, Romance

Actor: Brian Freeman, Camille Paglia, Cheryl Clarke, Cheryl Dunye, David Rakoff, Guinevere Turner, Irene Dunye, Lisa Marie Bronson, Sarah Schulman

Director: Cheryl Dunye

As impressive as Studio Ghibli’s collection of films are, I am still stubborn to believe that Porco Rosso is its most underrated film. Porco Rosso, directed by Hayao Miyazaki, is the story of a World War military aviator-turned-bounty hunter who has mysteriously been transformed into a pig. 

Bright with humor, heart, and flight (Miyazaki is largely influenced and inspired by the art of aviation), Porco Rosso manages to also acknowledge and reckon with the horrors of war. It also boasts one of, if not the greatest, line in any Ghibli film: I’d rather be a pig than a fascist.

Genre: Adventure, Animation, Comedy, Drama, Family

Actor: Akemi Okamura, Akio Otsuka, Bunshi Katsura, Bunshi Katsura Vi, Hiroko Seki, Mahito Tsujimura, Minoru Yada, Osamu Saka, Reizō Nomoto, Sanshi Katsura, Shûichirô Moriyama, Tokiko Kato, Tsunehiko Kamijo, Yoko Soumi, Yu Shimaka

Director: Hayao Miyazaki

Rating: PG

An absolute delight of a gem starring a young Winona Ryder as well as an amazing cast. Arguably Jim Jarmusch's best film, it tells the story of 5 different places at night from the perspective of cab drivers and their passengers: Los Angeles, New York, Paris, Rome, and Helsinki. It's really hard to pick a favorite among the stories, from a messy tomboy having to deal with a busy businesswoman, to a blind woman in Paris making a frustrated driver from Ivory Coast go insane. But look out for Helmut and Yo-Yo, from the New York story. I've rarely seen anything in film as fun as their story.

Genre: Comedy, Drama

Actor: Armin Mueller-Stahl, Béatrice Dalle, Eija Vilpas, Emile Abossolo M'bo, Gena Rowlands, Giancarlo Esposito, Gianni Schettini, Isaach De Bankolé, Jaakko Talaskivi, Kari Väänänen, Klaus Heydemann, Lisanne Falk, Matti Pellonpää, Paolo Bonacelli, Pascal N'Zonzi, Richard Boes, Roberto Benigni, Romolo Di Biasi, Rosie Perez, Sakari Kuosmanen, Stéphane Boucher, Tomi Salmela, Winona Ryder

Director: Jim Jarmusch

Rating: R

You live in a strange world. Or at least, that's what the generation before you thinks. Eight Grade is a movie that follows a girl going through her generation's strange world. Social media, selfies, Youtube; you name it. But also, the weight of her expectations (as shaped by the internet) versus her reality. Written and directed by famous comedian Bo Burnham, it's a gentle and often funny look at our anxieties and how they shape our growth. Prepare for a lot of cringes.

Genre: Comedy, Drama

Actor: Andrew Geher, Brenna Parker, Catherine Oliviere, Daniel Zolghadri, Deborah Unger, Dylan Vonderhorst, Elsie Fisher, Emily Robinson, Frank Deal, Fred Hechinger, Gerald Jones, Greg Crowe, Imani Lewis, J. Tucker Smith, Jake Ryan, Jalesia Martinez, Josh Hamilton, Kendall Seaman, Kevin R. Free, Kylie Seaman, Luke Mulligan, Luke Prael, Marguerite Stimpson, Missy Yager, Natalie Carter, Nora Mullins, Phoebe Amirault, Shacha Temirov, William Koo

Director: Bo Burnham

Rating: R

There’s a lot to think about in Dream Scenario, which posits the possibility of collectively seeing the same real man in your dreams. Norwegian filmmaker Kristoffer Borgli drops the painfully ordinary Paul (Cage) in an extraordinary reality to show us how easily one can spiral into insanity, how dangerous groupthink can be, how fickle cancel culture is, and how anything can happen to anyone, even to someone as unsuspecting as Paul. But Borgli doesn’t just experiment with ideas here, he also expertly plays with sounds and transitions, sometimes even cutting a scene before someone is done talking, to capture the skittish and unreliable language of dreams. More impressively, he takes into account how this phenomenon would play in our real, profit-oriented world. The capitalistic urge to make Paul an advertising tool, for instance, or to create tech that makes it possible for others to appear in dreams too, is both uncanny and depressingly realistic. Some might feel that Borgli is biting off more than he can chew but there’s a balance and ease to Dream Scenario that makes it feel inevitable. That’s thanks to Borgli’s brilliant direction but also, in no small part, to Cage’s inspired performance as a pathetic but harmless loser.

Genre: Comedy, Fantasy, Horror, Science Fiction

Actor: Agape Mngomezulu, Al Warren, Amber Midthunder, Ben Caldwell, Conrad Coates, David Klein, Domenic Di Rosa, Dylan Baker, Dylan Gelula, James Collins, Jennifer Wigmore, Jeremy Levick, Jessica Clement, Jim Armstrong, Jordan Raf, Josh Richards, Julianne Nicholson, Kaleb Horn, Kate Berlant, Krista Bridges, Lily Bird, Lily Gao, Liz Adjei, Maev Beaty, Marc Coppola, Marnie McPhail, Michael Cera, Nicholas Braun, Nicolas Cage, Nicole Leroux, Nneka Elliott, Noah Centineo, Noah Lamanna, Philip van Martin, Ramona Gilmour-Darling, Richard Jutras, Sofia Banzhaf, Star Slade, Stephen R. Hart, Tim Meadows, Will Corno

Director: Kristoffer Borgli

Rating: R

"California Dreamin'" by the Mamas and the Papas. You will fall in love with that song (if you haven't already) after watching this movie. Two stories, entangling into one; both about Hong Kong policemen falling in love with mysterious women. It was recommended by my friend after I said I loved Frances Ha. I don't know whether you can call this as offbeat romance.. but to me it was, and it's well worth the watch.

Genre: Comedy, Drama, Romance

Actor: Brigitte Lin, Chen Jinquan, Faye Wong, Jimmy Wong Chi-ming, Kwan Lee-Na, Lee-na Kwan, Liang Zen, Lynne Langdon, Piggy Chan Kam-Chuen, Rico Chu, Rico Chu Tak-On, Songshen Zuo, Takeshi Kaneshiro, Tony Chiu-Wai Leung, Tony Leung Chiu-Wai, Valerie Chow, Vickie Eng, Wong Chi-Ming, Zhiming Huang

Director: Kar-Wai Wong, Wong Kar-wai

Rating: PG-13

Probably the weirdest film you'll ever see. Paul Dano plays a borderline suicidal man who befriends a farting corpse that washed up from the sea as played by Daniel Radcliffe. It's an adventurous, witty and hilarious film yet it is filled with discreet and very deep lessons about society and norms. The soundtrack is so charmingly unique as well, it's a definite must-watch for anyone looking for a refreshing comedy.

Genre: Adventure, Comedy, Drama, Fantasy, Romance

Actor: Aaron Marshall, Andy Hull, Antonia Ribero, Daniel Radcliffe, Jessica Harbeck, Marika Casteel, Mary Elizabeth Winstead, Paul Dano, Richard Gross, Shane Carruth, Timothy Eulich

Director: Dan Kwan, Daniel Kwan, Daniel Scheinert

Rating: R

Generation-centric comedy is often of the “kids these days” variety — in which comedians make uninspired jibes about the youth of today while spectacularly lacking self-awareness of their own — but twenty-something stand-up Leo Reich thankfully upends that trend with his self-lampooning debut show. Reich takes a risk by unabashedly casting himself as a self-absorbed nepo baby in the opening — narcissism as a bit can become grating pretty quickly — but his perceptive abilities and readiness to both embody and commentate on Gen Z stereotypes are the saviors of this hour-long comedy special.

Stand-up isn’t the only medium he makes use of: the show is also part-musical, as Reich belts out wry musings on the contradictions of his generation — at once self-loathing but tending towards narcissism, cripplingly self-aware but no more enlightened for it — at intervals throughout. If there’s anything to lament here, it’s that Reich’s main character syndrome is so effectively paired with the doom-and-gloom context he paints (as he puts it, he’s spent way too much of his youth Googling "death toll") that the show’s aftertaste is a little too bitter — but then again, nihilism is another characteristic typically associated with zoomers, so you could argue this is simply supreme commitment to the bit.

Genre: Comedy

Actor: Leo Reich

Director: Thomas Hardiman

Rating: R

If you're a fan of musical theater of any kind, Topsy-Turvy pays tribute to that notoriously tricky art form with a stunning attention to detail and a dedication to telling its story without any unnecessary drama whatsoever. It's hard not to get swept up in the humor, entertainment, and simple joy found in the writing process and in rehearsals of entire scenes. Come for the Oscar-winning costumes and makeup, stay for the wonderfully old-timey musical numbers, the brilliantly grounded performance from Jim Broadbent, and the sense of satisfaction of just watching everything finally come together to thunderous applause.

Genre: Comedy, Drama, History, Music

Actor: Adam Searles, Akemi Otani, Alison Steadman, Allan Corduner, Andy Serkis, Angela Curran, Anna Francolini, Ashley Artus, Ashley Jensen, Bríd Brennan, Cathy Sara, Charles Simon, David Neville, Debbie Chazen, Dexter Fletcher, Dorothy Atkinson, Eiji Kusuhara, Eleanor David, Eve Pearce, Francis Lee, Gary Yershon, Gemma Page, Geoffrey Hutchings, Heather Craney, Jim Broadbent, John Warnaby, Jonathan Aris, Julia Rayner, Julian Bleach, Kacey Ainsworth, Kate Doherty, Katrin Cartlidge, Keeley Gainey, Kenneth Hadley, Kevin McKidd, Lavinia Bertram, Lesley Manville, Lorraine Brunning, Louise Gold, Mark Benton, Martin Savage, Mary Roscoe, Matt Bardock, Matthew Mills, Mia Soteriou, Michael Simkins, Michelle Chadwick, Monica Dolan, Naoko Mori, Nicholas Boulton, Nicholas Woodeson, Nick Bartlett, Paul Barnhill, Paul Rider, Richard Attlee, Richard Coyle, Roger Heathcott, Ron Cook, Rosie Cavaliero, Sam Kelly, Sarah Howe, Shirley Henderson, Sophie Duval, Stefan Bednarczyk, Steve Speirs, Sukie Smith, Teresa Gallagher, Theresa Watson, Timothy Spall, Togo Igawa, Vincent Franklin, Wendy Nottingham

Director: Mike Leigh

Before “burnout,” “bullshit jobs,” and “quiet quitting” became part of our everyday lexicon, there was a film in the ‘90s that prophesied the rise of these workplace problems. Office Space follows three co-workers who, having had enough of their dreary low-paying jobs, fight back against their company via an embezzlement scheme. 

Office Space makes the most out of its indie budget as it mostly takes place in the cramped quarters of a company, effectively bottling us into the cubicled windowless world of the characters. But the real beauty of the film is in the details, from its quick zingers and thoughtful takes on the essence of work down to its elaborate “planning to plan” scheme in the background and the employees’ forced politeness singing happy birthday to their boss. Modern viewers will notice that Office Space sits right in between the dystopian thriller Severance and the beloved sitcom The Office—a dark comedy that highlights the necessity of humanity in everyday work. 

Genre: Comedy, Drama

Actor: Ajay Naidu, Alexandra Wentworth, Ali Wentworth, Barbara George-Reiss, Charissa Allen, David Herman, Diedrich Bader, Gabriel Folse, Gary Cole, Greg Pitts, Jack Betts, Jackie Belvin, Jennifer Aniston, Jennifer Jane Emerson, Jesse De Luna, Joe Bays, John C. McGinley, Kinna McInroe, Kyle Scott Jackson, Michael McShane, Mike Judge, Orlando Jones, Paul Willson, Richard Riehle, Ron Livingston, Rupert Reyes, Spencer Kayden, Stephen Root, Todd Duffey, Tom Schuster

Director: Mike Judge

Rating: R

Most computer screen films take the horror film route as a cautionary tale about technology and how we use it. However, when the world was on lockdown, one screenlife film takes a look at its positive side. Simple, straightforward, and comforting, Language Lessons celebrates technology as a means for connection. Through surprise Spanish lessons purchased by his husband, Adam (Mark Duplass) forms a friendship with his instructor Cariño (Natalie Morales). At times, watching the film feels like listening into someone else’s Zoom call, however, their back-and-forth feels engaging because of Morales and Duplass’ chemistry. And when loss hits, on both sides, it’s only natural that their relationship deepens as they console each other. Expressive without being melodramatic and intimate without being too pushy, Language Lessons is a rare optimistic take towards the way we connect to each other through technology.

Genre: Comedy, Drama, Romance

Actor: Desean Terry, Mark Duplass, Natalie Morales

Director: Natalie Morales

Rating: Not Rated

A fun science fiction movie from the UK,  Frequently Asked Questions About Time Travel stars Chris O'Dowd and Anna Faris. The plot centers around two geeks and their cynical friend who go out for a couple of pints and end up having a night they won't soon forget. To go any deeper would court spoilers, but suffice to say there is time travel, witty banter, hilarious scenes and just an all-around good time.

Genre: Comedy, Drama, Romance, Science Fiction

Actor: Anna Faris, Arthur Nightingale, Chris O'Dowd, Dean Lennox Kelly, John Warman, Marc Wootton, Meredith MacNeill, Ray Gardner

Director: Gareth Carrivick

Rating: Unrated

Watch this if you like weird movies. And don't be fooled by the first half, which serves just to set Jesse Eisenberg's character and the monotone life he leads. It's the calm before the storm, during which that character is attacked by a violent gang and decides to take self-defense classes in an unusual club. This is a movie about modern manhood and how it can lead to some pretty strange situations. Great performance from Eisenberg as usual.

Genre: Action, Comedy, Drama, Thriller

Actor: Alessandro Nivola, Apollo Bacala, Caroline Amiguet, Dallas Edwards, Davey Johnson, David Zellner, Frederic Spitz, Hauke Bahr, Imogen Poots, Jason Burkey, Jesse Eisenberg, Josh Fadem, Katherine Smith-Rodden, Leland Orser, Lena Friedrich, Louis Robert Thompson, Mike Brooks, Phillip Andre Botello, Steve Terada

Director: Riley Stearns

Rating: R

It’s very interesting, if not startling, to see an earnest movie made about the white upper class these days. Metropolitan is one such film, and even though it was released in the ’90s, it still stands the test of time precisely because it neither judges nor defends the group of WASPs it follows. It simply shows them in all their elegance and sophistication, as well as their insulation and irony. 

Metropolitan takes place in the upper crust of New York debutante society, during Christmas vacation, where soirees are rampant and afterparties even more so. The young-adult leads who navigate the scene in their expensive clothes and self-important aura recall a Scott Fitzgerald novel, or if you like, Gossip Girl episode. But instead of falling into tragedies, these characters just end up in silly but relatable mishaps and misunderstandings: they’re just kids after all. And as high and mighty as they may seem, whiling away in tall Park Avenue apartments, they’re still prone to the universal pains that haunt and shape teenagers. Expect to see heartbreak, jealousy, and longing even among the brightest and wealthiest of New York. 

Genre: Comedy, Drama, Romance

Actor: Alice Connorton, Carolyn Farina, Chris Eigeman, Donal Lardner Ward, Francis Creighton, Isabel Gillies, Taylor Nichols, Thomas R. Voth, Will Kempe

Director: Whit Stillman

Rating: PG-13